Octaminomycins A and B, cyclic octadepsipeptides active against Plasmodium falciparum

Jun Pil Jang; Toshihiko Nogawa; Yushi Futamura; Takeshi Shimizu; Daisuke Hashizume; Shunji Takahashi; Jae Hyuk Jang; Jong Seog Ahn; Hiroyuki Osada

doi:10.1021/acs.jnatprod.6b00758

Octaminomycins A and B, cyclic octadepsipeptides active against Plasmodium falciparum

Jun Pil Jang, Toshihiko Nogawa, Yushi Futamura, Takeshi Shimizu, Daisuke Hashizume, Shunji Takahashi, Jae Hyuk Jang, Jong Seog Ahn^*, Hiroyuki Osada

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

Two new cyclic octadepsipeptides, octaminomycins A (1) and B (2), were isolated from a microbial metabolite fraction library of Streptomyces sp. RK85-270 based on Natural Products Plot screening. Their structures were elucidated on the basis of HRESIMS, 1D and 2D NMR spectroscopic data, and MS/MS experiments for sequence analysis. The absolute configurations of the constituent amino acid residues were determined by a combination of single-crystal X-ray diffraction and Marfey's methodology. Notably, octaminomycins A (1) and B (2) showed good in vitro antiplasmodial activity against chloroquine-sensitive as well as chloroquine-resistant strains with no cytotoxicity up to 30 μM. (Chemical Equation Presented).

Original language	English
Pages (from-to)	134-140
Number of pages	7
Journal	Journal of Natural Products
Volume	80
Issue number	1
DOIs	https://doi.org/10.1021/acs.jnatprod.6b00758
Publication status	Published - 2017 Jan 27
Externally published	Yes

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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title = "Octaminomycins A and B, cyclic octadepsipeptides active against Plasmodium falciparum",

abstract = "Two new cyclic octadepsipeptides, octaminomycins A (1) and B (2), were isolated from a microbial metabolite fraction library of Streptomyces sp. RK85-270 based on Natural Products Plot screening. Their structures were elucidated on the basis of HRESIMS, 1D and 2D NMR spectroscopic data, and MS/MS experiments for sequence analysis. The absolute configurations of the constituent amino acid residues were determined by a combination of single-crystal X-ray diffraction and Marfey's methodology. Notably, octaminomycins A (1) and B (2) showed good in vitro antiplasmodial activity against chloroquine-sensitive as well as chloroquine-resistant strains with no cytotoxicity up to 30 μM. (Chemical Equation Presented).",

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T1 - Octaminomycins A and B, cyclic octadepsipeptides active against Plasmodium falciparum

AU - Jang, Jun Pil

AU - Nogawa, Toshihiko

AU - Futamura, Yushi

AU - Shimizu, Takeshi

AU - Hashizume, Daisuke

AU - Takahashi, Shunji

AU - Jang, Jae Hyuk

AU - Ahn, Jong Seog

AU - Osada, Hiroyuki

PY - 2017/1/27

Y1 - 2017/1/27

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AB - Two new cyclic octadepsipeptides, octaminomycins A (1) and B (2), were isolated from a microbial metabolite fraction library of Streptomyces sp. RK85-270 based on Natural Products Plot screening. Their structures were elucidated on the basis of HRESIMS, 1D and 2D NMR spectroscopic data, and MS/MS experiments for sequence analysis. The absolute configurations of the constituent amino acid residues were determined by a combination of single-crystal X-ray diffraction and Marfey's methodology. Notably, octaminomycins A (1) and B (2) showed good in vitro antiplasmodial activity against chloroquine-sensitive as well as chloroquine-resistant strains with no cytotoxicity up to 30 μM. (Chemical Equation Presented).

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Octaminomycins A and B, cyclic octadepsipeptides active against Plasmodium falciparum

Abstract

ASJC Scopus subject areas

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